The dead guy, Marten Santos, had been notoriously rich and depraved while he was alive. He had never tried to pass as righteous, though, never pretended to be perfect. We all knew about his peculiar tastes and erratic passions, and loved him for that. Nevertheless, he’d been raised a strict Roman Catholic and so the funeral was a stuffy, conservative affair, held at Our Lady of Divine Sorrows. After the funeral, as the teary-eyed pallbearers removed the casket from the church and solemnly loaded it into the back of the hearse, Our Lady’s bell tolled mournfully, sounding all the more poignant in the gray drizzle of rain. He was a man who was going to be missed by a lot of good people.
In life, Mr Santos had been one of my favorite tricks. When he died suddenly of a heart attack three days ago, the newspaper said that he was pushing seventy. During the year when he’d been one of my regulars, he claimed to be fifty-five. It says a lot that after all these years I was moved enough by a sense of loss to attend his funeral. But then, he hadn’t always been a trick. With Mr Santos, I’d done the unthinkable and allowed a favorite john to become a lover, or nearly so. The shame of that slip-up on my part, and a difficult scene he put me through in a cheap hotel room, had caused us to part on uncomfortable terms. Still, it made me no less fond of him.
I don’t turn tricks anymore, I haven’t for years. I’m almost forty now. I work in a respectable office and I earn a respectable living. I present a very hard-assed, successful-bitch version of myself to the world and it’s helped me to succeed and keep my past where it should be, in the past. The frantic, frenetic survival skills acquired by all New Yorkers makes the town a forgiving place. As long as you don’t wind up at the heart of a sordid public scandal in a court of law, where New Yorkers show their ugly sides and revel in seeing your past mistakes slung at you like so much mud, you can do just about anything to get ahead in this town and not have to worry too much that it’ll come back to haunt you.
Mr Santos and I first met in an upscale espresso shop on the Upper East Side. This was back in the 80s, when a whole lot of people had money to burn. Mr Santos was friends with the owner, Hajid, who was one of my regulars, too. Hajid liked getting blow jobs behind the desk in his office. His office was in the basement of the coffee house. It was decidedly downscale in that dark, damp, vermin-infested cellar. However, a simple blow job, as long as I was willing to have my pants around my knees and keep my naked ass out for his viewing pleasure, lasted only about ten minutes and garnered me two hundred tax-free dollars, so I found ways to make even that ratskeller seem erotic.
The evening I met Mr Santos, I was actually just having coffee. I wasn’t engaged in business. Hajid and I were on friendly terms. He introduced me to Mr Santos, with a nod and a wink, and Mr Santos pulled up a chair. He got right down to the business of getting to know me better. He ended the meeting by paying my modest tab and then asking me for my phone number, which of course I gave him since it was obvious he was loaded – even more so than Hajid.
Our trysts started out simple and straightforward. Mr Santos would always arrange for me to meet him in other rich people’s high-class apartments. The people he knew went on extended vacations, traveled on business to faraway places, or had primary homes in other countries. Mr Santos was married back then, and apparently he and his other married male friends formed a cozy circle of infidels, each leaving the rest of the crew a key to his empty apartment for extramarital liaisons in his absence. I don’t think the wives ever had a clue what was taking place in the sanctity of their homes while they were off on holiday.
I was never to touch anything, never allowed to get too comfortable in the jaw-dropping luxury of our trysting places. Mr Santos liked anal and that was pretty much the sole basis of our get-togethers, at first. Without fanfare, he would unzip his trousers; let them fall unceremoniously to his ankles, along with his boxers. He’d slip on a rubber; slather it with the lube that he carried in his pocket in handy individual foil packets. Then I’d bend over anything steady and he’d slide his cock up my ass.
He fucked me like a man who had important meetings to get to, so he usually came pretty quickly. I didn’t have to say anything weird, or dress in anything unusual. I simply had to show up with an absolutely clean asshole, bend over and let him ream me; that was all he required. For that, I got five hundred dollars cash; five crisp, one-hundred-dollar bills, folded in the middle, which he’d place under my nose while I was still bending over – before he’d even pulled his cock out of me, I’d get paid.
There was something about the way he paid me that tended to make me feel a little humiliated, but he didn’t seem to think twice about it. By the time I’d turn around, he’d have the used condom off, his trousers pulled up, and would be heading to the toilet to flush the condom down. He never said anything like. “Here’s your money you whore,” or “Take that, bitch.” He just had a funny habit of leaving it parked under my nose while my ass was still stuffed with him.
I remember when we had our first real conversation. It was a day when he seemed to be at leisure. He wasn’t pressed for time, wasn’t hurrying. It was a day when he wandered around the spacious apartment we were using, looking for the perfect place to bend me over, making small talk, making jokes. “Bend over that chair there, let me see the view. Pull up your skirt. No, we can find something better.”
When he finally decided on the perfect spot – an ergonomically correct artist’s stool – he lifted my skirt himself, pulled my panties down (an intimate gesture he’d never once done before) and then said, “You know what this reminds me of?”
My naked ass in the air, my thighs spread in anticipation, my head hanging down, I said, “No, what?”
“Church. This reminds me of church.”
He didn’t elaborate and I had no idea what he was talking about. But the thought of church seemed to make him feel even more jovial. He sank to his knees and rimmed me, his hot, wet tongue expertly stroking my puckered hole. It felt sensational. I actually moaned and felt like touching myself.
Having his nose in my ass seemed to arouse his passion, for that day he fucked my ass especially vigorously, nearly knocking me off the stool several times. The mounting pressure of his thickening hard-on sucking in and out of my ass made me cry out. When he came, he pulled his cock out a little aggressively, gave me a resounding smack on my upturned ass, and said, “Here you go. Thanks, kiddo.” And the money was once again placed in front of my face – on this occasion, I’d been staring at a parquet floor.
His breezy pre-sex conversing, combined with his sudden rugged manner with me during sex, made me see Mr Santos in a different light. He was a handsome man, I decided, as I watched him zip up his trousers and go off in search of the toilet. I still had my panties around my knees when he came back into the room. I was lingering in my little swoon.
“What’s with you?” he asked.
Snapping out of it and feeling embarrassed, I moved to pull up my panties.
“No, wait.” He stopped me. “Not yet. You feel like making a little extra money today?”
I was caught off guard. He fished out his wallet and surveyed its contents. “Well, I have ten whole dollars.” He found this amusing. “What do you feel like doing for ten dollars?”
“What did you have in mind?”
“I want to try something and see if I can make you come.”
I never, under any circumstances, came with a trick. But Mr Santos intrigued me. “You think you can make me come for ten dollars?”
“Ten bucks, and a nice dinner. What do you say to that? My wife’s out of town and I’ve got all the time in the world. I’ll make it up to you next time about the money. You know I’m good for it.”
I was feeling game. I liked Mr Santos. I wasn’t worried about the money.
He told me to step out of my panties completely, then to squat down on the parquet floor. He told me that under no circumstances should I touch myself; he wanted to do all the work. He lubed two of his fingers, squatted down next to me, held m
e around my shoulders to sort of brace me, and then he stuck the two lubed fingers up my ass. He wiggled them vigorously in there, pushing hard against my perineum, rubbing the wall of muscle with all his strength.
“Oh god,” I squealed in sheer ecstasy, clutching him tight, a stream of piss suddenly squirting out of me and forming a puddle on the nice wood floor.
“Go for it, baby. Let everything go. We can clean this up later. Bear down on me.”
I did as he suggested, pushing my asshole down around his hardworking fingers, never dreaming that I could be launched into orgasm like a rocket without direct pressure applied to my clit. But it happened. My thighs shook as I squatted and bore down, more fluids gushing out of my open pisshole. My body was overwhelmed by waves of pleasure as his fingers rubbed more vigorously against the pressure of my now frantically contracting sphincter.
When I was through hyperventilating and convulsing like a lunatic, Mr Santos was still holding me, smiling. “Did you come?” he asked, very pleased with himself.
I didn’t take the extra ten dollars that day, but I took him up on his offer to buy me dinner and that was the beginning of a new chapter in our “business relationship.”
He continued to pay me whenever we got together, but we talked more, he took more time with me, he felt challenged to give me orgasms in unexpected ways. Soon, he was paying for rooms in five-star hotels, where we’d disappear for entire days together, relying on room service for sustenance. He introduced blindfolds, light bondage, and spanking to the list of things we were now doing with each other regularly in a lavish king-sized bed.
“Do you ever eat pussy?” he asked me one afternoon. “I mean, do you ever get asked to do that when you’re out on a calls?”
I looked at him uneasily, not at all pleased that the world of my other tricks was even remotely entering into our time together.
“Do you even know how to eat pussy?”
“Of course I do.”
“You get paid to do that?”
“Sometimes.” I didn’t feel much like discussing it.
“I’d like to see you eat pussy, you know that?”
You and every other trick on earth, I told myself. The last thing I wanted was to bring another girl into our scene, a girl who might prove to be more novel than me, a girl who might walk off with his number in her purse and then I would lose my favorite trick. Mr Santos was now the man I fantasized about when I was home alone in bed. I didn’t think he would leave his wife for me, or anything like that, but I naively considered us lovers. I’d begun to hate the fact that he still paid me.
“What’s that face for?” he said. “You aren’t into pussy?”
“Girls are all right.”
“I was thinking more along the lines of a woman – not a girl.”
He immediately piqued my interest. “You mean you have someone in mind?”
“To be honest, there’s a woman I’ve been seeing off and on for years, since before I was married. Occasinally, we get together when our spouses are otherwise detained and we have sex. I told her about you. How much fun you are. How amenable you can be.”
And whose idea was it to make it a threesome, I wondered suspiciously, hers, or his?
“She’ll pay you the same amount I do; you’ll get double your usual fee. It wouldn’t be a question of taking advantage. I would really like to see you eat her pussy. And I think she has an idea of a scene of her own. She’s very willing to pay you,” he repeated. “I don’t think she’s ever paid anyone to do a scene with her. Or to have any kind of sex with her, for that matter. She’s just a regular married woman, but a good friend of mine.”
She sounded harmless enough. But you’d think after my years of turning tricks. I would have known beyond a doubt that people who sound harmless can be the most difficult customers when it’s all said and done.
Still, I agreed to do the three-way. We made an appointment for an afternoon the following week. For some reason, we were meeting in a tacky hotel in midtown – gone was the luxury of the king-sized bed, the crisp white sheets and room service. Everything about the hotel they’d chosen was dingy, seedy, and low class.
Mr Santos had asked me to bring along an outfit that would be suitable for a naughty little girl routine. Even though I’d never gone to Catholic school myself, I had a vintage Catholic schoolgirl uniform that fit me perfectly. I figured Mr Santos would get off on the religion thing so that’s what I packed for my change of clothes.
I’d been getting steadily more into the idea of the three-way as the day approached. Anything that involved the unpredictability of Mr Santos’s lusty libido aroused my own sexual appetites. He was nothing like an average trick. So when I knocked on the hotel room door that afternoon, I was already horny, already sopping wet between my legs. Until Mr Santos let me into the room and introduced me to his woman friend.
Oh my god, I realized in sick horror, it’s Mrs Hamilton.
She’d been my tenth grade sociology teacher. A woman who’d made my life a living hell for an entire year. I was certain it was her. To this day, I don’t know if she recognized me, too. If she did, she never once let on. But I knew it was her. She was simply using a fake name, like a lot of tricks do.
“Call me either ‘Daddy’ or ‘Sir’ today,” Mr Santos was instructing me. “And this is your new stepmother, Louise.”
Louise? They couldn’t come up with anything less corny than Louise?
I had that feeling of panic in my gut that I used to get in my early days of hustling; I wanted to bolt. But then I focused on the money: one thousand dollars cash for a single afternoon’s work. It would be worth it. But I saw immediately that it was going to be just that – work.
Mrs Hamilton had never been an unattractive woman; it was just that she’d always been a mean bitch of a teacher. In my years since high school, she’d managed to stay attractive; she’d taken good care of herself. I figured that if she knew Mr Santos, she must have money, too, and that always helps women stay good-looking. Yet it made me wonder why she’d chosen to teach at all. Perhaps for the sick thrill of tormenting teenagers?
“Louise wants to help you change clothes,” Mr Santos told me. “It’ll give you two a chance to get comfortable with each other. I’m going to run across the street to the liquor store. This trashy hotel doesn’t even supply booze.”
Shit. He was leaving me alone with her. The dreaded moment was starting to look even worse. Not only would I have to get naked for Mrs Hamilton, I would have to be completely alone with her while it happened. No horny Mr Santos around to use as a buffer zone.
When he was gone, she went right into “efficient teacher” mode. “Come here,” she said flatly. “Let’s get you out of those clothes and into something more appropriate.”
She didn’t act like it made her at all nervous to be around a prostitute, to be doing a scene. I wondered if she was anybody’s horny lesbo stepmother in real life. The implications of that thought creeped me out. I had to force myself to keep my mind a blank.
Mrs Hamilton was going through my bag, pulling out my change of clothes. She seemed to recognize the uniform for what it was – something real girls wore in real high schools. “Are you Catholic?” she asked. “Not that it’s any of my business.”
“Yes,” I said. “But I went to public schools.” The sudden rudeness in my tone surprised even me.
She eyed me coolly, taking in that last remark. “Come over here,” she said.
Shit. She was actually making me nervous. But I went over to her. Without hesitating, she began undressing me. “Let me tell you something,” she explained carefully, unbuttoning my shirt with manicured fingers. “While we’re in the confines of this room, while we’re on the clock, so to speak, I have no qualms whatsoever about making it very clear which one of us is on top.” The sound of her words alone felt like a slap. She had my shirt off. She was moving to unfasten my bra then, her fingers were touching the skin on my back, her face was close to mine. I didn’t
like it. “If you want to keep talking to me in that rude tone,” she continued, “go right ahead. But consider yourself warned. I’m not afraid of girls like you. I deal with your kind every day.”
My bra was off. My tits were right there in front of her, my nipples shivering to stiff points from the sudden change in temperature. How many times had I bared my tits for strange clients? But this took the cake for strangeness. I felt exposed.
She didn’t touch me, though. She barely even paused to look at my nakedness. She was already on to my tight jeans, unzipping them, tugging them down to my ankles.
I was in that state of half-undressed nervousness when Mr Santos came back to the room, carrying a fifth of gin and a large carton of Tropicana OJ.
Jesus, I wondered, how trashy are we going to get? Where was the top-shelf bourbon, or at the very least, some cheap champagne?
“Well,” he said, regarding us with satisfaction, “we’re certainly progressing here. Anyone want a drink?”
We all did. Mr Santos played bartender while keeping a keen eye on us.
Mrs Hamilton had me completely undressed, except for my panties. Those she seemed to want to take more time with. She lowered them slowly, anticipating the unveiling of my neatly trimmed snatch. She was actually squatting down in front of me, apparently wanting an up close and personal view. It made me even more uncomfortable – not so much that Mrs Hamilton was squatting down in front of me, so obviously aroused by the imminent sight of another woman’s pussy, but the fact that I was getting off on it, too. I was suddenly wet again.
“Good lord,” she said quickly under her breath. She’d peeled my panties past my mound, rolled them partially down my thighs and seen the strand of gooey wetness connecting my soaking hole to the cotton crotch of my underwear. She looked up at Mr Santos, who was now standing next to us, offers of drinks in his hands. “She’s so wet,” Mrs Hamilton explained in quiet earnestness, as if the sight of a twat swollen in arousal pained her deliciously.
The Mammoth Book of Erotica presents The Best of Marilyn Jaye Lewis Page 9
